Solid-Phase Synthesis of Aza-Proline Analogs of GHRP-6

摘要

Incorporation within the peptide sequence of an aza-amino acid, in which the alpha-carbon is substituted for a nitrogen atom, has been shown to induce a β-turn conformation as a direct consequence of lone pair - lone pair repulsion [1]. Particularly, aza-proline has been shown to enhance cis-amide conformation, thereby favoring type VI β-turns [2] (Figure 1). Whereby native GHRP-6 shows affinity for both the CD36 and GHS-R1a receptors, [3] AzaProcontaining GHRP-6 azapeptide analogs were anticipated to introduce conformational rigidity that could allow for preferential binding towards the CD36 receptor, and constituted promising targets for the treatment of angiogenesis related diseases.